Triphenylphosphine → (2-(Benzyloxy)-4,5-difluorophenethyl)triphenylphosphonium iodide salt

HRID 921186Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[CH2:17][CH2:18][I:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]1[CH:25]=[CH:24][C:23]([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1>C1(C)C(C)=CC=CC=1>[I-:19].[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[CH2:17][CH2:18][P+:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:23]1[CH:22]=[CH:21][CH:20]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 1-(benzyloxy)-4,5-difluoro-2-(2-iodoethyl)benzene (630 mg, 1.684 mmol) in xylene (10 mL) was added Ph3P (883 mg, 3.37 mmol) and the mixture was heated at 140° C. for 16 h. The mixture was cooled to rt (The product solidified). Solids were then filtered off and washed with ether and hexane, dried under high vacuum to afford (2-(benzyloxy)-4,5-difluorophenethyl)triphenylphosphonium iodide salt (850 mg, 1.336 mmol, 79% yield) as white solid. 1H NMR (500 MHz, CDCl3)) δ 7.87-7.61 (m, 15H), 7.44-7.33 (m, 6H), 6.74 (dd, J=11.6, 6.4 Hz, 1H), 5.00 (s, 2H), 3.94-3.83 (m, 2H), 3.06-2.91 (m, 2H). LCMS (M+H)=510.4.

Workup

temperatureThe mixture was cooled to rt (The product
filtrationSolids were then filtered off
washwashed with ether and hexane
customdried under high vacuum

Sources & evidence

ORD record: ord-e94292513c5043a280e99d5fbde5b33a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273067B2

Reaction notes

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